In the previous post, we saw that amides can be reduced to amines by LiAlH4: Let’s see how tertiary amides can be reduced to amines and aldehydes using alkyboranes. Reduction of Amides by Alkylboranes The reduction of amides … Read more
In this post, we will discuss the reduction of carboxylic acids and their derivatives, such as acid chlorides, esters, amides, and nitriles. Let’s start with carboxylic acids. Reduction of Carboxylic Acids Carboxylic acids can be converted to alcohols using … Read more
There are a few ways of converting carboxylic acids to esters, and the first one is the direct reaction between the acid and an alcohol. This is known as the Fischer esterification which is a type of addition-elimination reaction of … Read more
Let’s discuss how esters can be converted to aldehydes. In the previous post, we saw that esters can be reduced to primary alcohols using a strong reducing agent such as LiAlH4: Now, we can of course oxidize the … Read more
We know that aldehydes and ketones react with one equivalent of Grignard reagents, producing secondary and tertiary alcohols, respectively. Esters, on the other hand, react with two equivalents of Grignard reagents, producing tertiary alcohols: What happens is we have … Read more
Carboxylic acids can be converted to alcohols using an excess of strong reducing agents such as LiAlH4. The excess reducing agent is needed because first we are going to have a deprotonation of the carboxylic acid, and … Read more
There are two main strategies we can use to convert alkyl halides to carboxylic acids: 1) Oxidizing the carbon connected to the halogen, 2) Introducing the COOH group, thus increasing the length of the carbon chain: For the … Read more
The Problems in Converting Esters to Ketones Esters are carbonyl compounds susceptible to nucleophilic additions, and one may think of converting them to ketones using Grignard, organolithium, or organocuprate reagents. However, the problem with those is that Grignard and organolithium … Read more
